Abstract
A simple and environmentally benign method for the preparation of 25-hydroxycholesterol, a modulator of cholesterol biosynthesis, has been developed. The final product can be obtained by the reaction of mCPBA and 24-dehydrocholesterol, followed by reduction with lithium aluminium hydride in THF in moderate yields.
References
1.
Shoujiro O.
,
Genta K.
,
Akina M.
,
Atsuko H.
,
Kuniko M.
,
Shigeo I.
,
Alan F.H.
, and
Takashi I.
, Steroids , 2009 , 74 , 81 .
2.
Nobuo I.
, Med. Res. Rev. , 1987 , 7 , 333 .
3.
Henbest H.B.
, and
Nicholls B.J.
, J. Chem. Soc. , 1959 , 41 , 227 .
4.
Elhihel L.
,
Charles G.
,
Letourneux Y.
, and
Ourisson G.C.R.
, Chimie , 2003 , 6 , 79 .
5.
Njimi T.
, and
Charles G.
, U.S. Patent 3803184 , 1974 .
6.
Swaminathan S.
,
Pinkerton F.D.
,
Numazawa S.
,
Wilson W.K.
, and
Schroepfer G.J.
, J. Lipid. Res. , 1992 , 33 , 1503 .
7.
Ernest L.E.
, and
Mark N.R.
, J. Am. Soc. Chem. , 1960 , 82 , 1362 .
8.
Brown W.G.
, Org. React. , 1951 , 6 , 469 .
9.
Parker R.E.
, and
Isaacs N.S.
, Chem. Rev. , 1959 , 59 , 737 .
10.
Idler D.R.
,
Saito A.
, and
Wiseman P.
, Steriods , 1968 , 11 , 465 .
11.
Dryuk V.G.
, Russ. Chem. Rev. , 1985 , 54 , 1674 .
12.
Nicholas C.O.
,
Tomkinson M.W.
, and
Timothy M.W.
, J. Org. Chem. , 1998 , 63 , 9919 .
13.
Masuo M.
,
Lightbourn J.R.
, and
Ikekawa N.
, Chem. Pharm. Bull. , 1973 , 21 , 457 .
14.
Dauben W.G.
, and
Bradlow H.L.
, J. Am. Chem. Soc. , 1950 , 72 , 4248 .
15.
Zhou X.D.
,
Zhen H.
, and
Zhou W.S.
, Chinese. Sci. Bull. , 2003 , 48 , 3247 .